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The personalities of leaders have been shown to impact the culture of their organizations and are also expected to have a more distal impact on the firm’s financial performance. However, the authors also expect that leader gender is an important intervening variable such that exhibiting various personality dimensions may result in unique cultural and performance-based outcomes for women and men leaders. Thus, the authors seek to examine first the impact of leader personality on organizational performance, as driven through organizational culture as a mediating mechanism. In doing so, the authors propose the expected impact of specific personality dimensions on certain types of organizational cultures, and those cultures’ subsequent impact on the organization’s performance. The authors then extend to consider the moderating effects of leader gender on the relationship between leader personality and organization. To support their propositions, the authors draw from upper echelons and implicit leadership theories. The authors encourage researchers to consider the proposition within a sample of the largest publicly traded US companies (i.e., Fortune 500) at an important era in history such that for the first time, 10% of these companies are led by women. In doing so, the authors hope to understand the leadership dynamics at the highest echelons of corporate governance and provide actionable insights for companies aiming to optimize their leadership composition and drive sustainable performance.